The 12 Wine Tasting Day Trips in Italy We Would Book First

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

Leave Florence by coach for Siena, San Gimignano, Pisa, and the Chianti countryside. You will tour Siena Cathedral and Piazza del Campo, eat at Fattoria Poggio Alloro, taste four wines, and explore the other towns independently. Guides such as Alex, Sara, Davide, and Manolo lead the day, which runs about 11 to 12 hours.

“Fun day but a lot to cover so be prepared to move fast. We saw all the highlights of Siena but had only about 30 minutes free time there to explore and shop. We had a little more than an hour free time in San Gimignano and in Pisa. This tour is alot of walking. I did over 18,000 steps. Tour guide, Sara, was very good. Super nice and easy to understand.”

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2.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

★★★★★★★★★★4.5 · 6,006 reviews · 12 hours (approx.) · from $78

Travel from Florence to Siena, San Gimignano, and Pisa with an English-speaking escort. Choose the guided Siena option and add a Tuscan winery lunch with wine pairing. Expect a 12-hour day, a large group, timed stops, plenty of walking, and a memorable look at Tuscany’s hill towns and famous monuments.

“It’s bilingual English and Spanish. A very large group! The guides managed everyone very well. The lunch and wine tasting was a great experience!”

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3.Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 5,232 reviews · 12 hours (approx.) · from $83

Travel from Rome to Montepulciano and Pienza in a small group of up to 25 people. You’ll tour Montepulciano, visit San Biagio, eat a three-course farm lunch, taste Tuscan wines including Brunello di Montalcino, and enjoy free time in Pienza. Guides such as Flavio, Barbara, Anna, and Antonino have led past departures.

“Great day trip. The views in Montepulicano were beautiful and got my photography fix. The lunch was delicious and enjoyed learning about the family history. Icing on the cake was the last town on Pirenze (spelling?) with more fabulous views. Would happily do it again. Our guide was great!”

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4.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Spend 12 hours exploring Tuscany by coach, with a guided walk in Siena, free time in San Gimignano and Pisa, and an optional organic winery lunch. Guides such as Sara, Alessandro, Giancarlo, and Manolo bring the history to life. Choose the lunch option for Chianti views, four regional wines, and a generous Tuscan meal.

“Sara was great! She was entertaining and knowledgeable. Our guide in Sienna was also incredible. She grew up there and lives there and knew all about local history and culture. 10/10!!!!”

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5.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Spend about 11 hours exploring medieval Tuscany by coach, with free time in San Gimignano and Monteriggioni, a three-wine tasting and Tuscan lunch at a Chianti winery, and guided Siena options including the striped cathedral and Piccolomini Library. Guides such as Sandro, Marta, Ricardo, and Ilaria have earned warm praise.

“Other reviews are correct- this is not a guided tour. However, I liked how we are on our own in each city rather than having to keep up with a guide and large group. Hilary was very sweet and gave us information about each city before exiting the bus. The winery was just a tasting experience (4 wines) with lunch. I thought they gave us a lot of food: bruschetta, meats, cheese, a full portion of pasta with ragu, and biscotti. Personally I was full after it. The employees there were very energetic and fun. Be prepared for a lot of walking. Uneven streets and hills. This tour is not…”

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6.Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77Best value

Travel from Florence to Pisa, San Gimignano, Chianti, and Siena by air-conditioned coach. You will see Pisa’s cathedral complex, medieval towers, Siena’s Piazza del Campo, and the cathedral. Add a three-course Tuscan lunch with three wines and Vin Santo, plus guided Siena visits. Guides such as Marta, Aaron, Sandro, and Federico are regularly praised for clear explanations and good organization.

“Great day out visiting some beautiful Tuscan locations. The lunch and wine tasting was really good. Our guide Martha gave good insights into the different locations and good tips on things to do and see. Thanks to our driver Silvio.”

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7.Chianti Wine Tastings at Sunset Day Trip

★★★★★★★★★★4.7 · 274 reviews · 5 - 7 hours · from $151

Travel from Florence into Chianti in a comfortable, air-conditioned minivan, stopping at Greve, Montefioralle, and scenic hilltop viewpoints. Visit two family-run wineries, tour their cellars, taste six wines with cheese, jam, and bruschetta, then add a countryside dinner at sunset. English- and Italian-speaking drivers such as Luigi, Simone, and Alaa lead the outing.

“Luigi was an amazing guide! 2 great wineries and a fantastic dinner to follow.”

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8.Ultimate Tuscany Day Trip with Wine & Lunch

★★★★★★★★★★4.8 · 221 reviews · 9 hours · from $229

Meet your English-speaking guide near the carousel in Piazza della Repubblica, then travel by air-conditioned minivan to San Gimignano, a Chianti family winery, and Siena. Expect free time in both towns, a seasonal lunch with wine pairings, and a full nine-hour day. Guides have included Sandra, Antonio, Alma, and Stefano.

“A lovely day in Tuscany! The transportation was ideal. Our group consisted of 10 people total traveling in two vans. We loved seeing Siena and San Gimignano. The highlight however was our visit to the winery. The lunch was incredible and our host was so welcoming. We loved trying the family wines. A very special experience.”

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9.Dolomites and Prosecco Hills Day Trip with Wine

★★★★★★★★★★5.0 · 117 reviews · from $214

Leave Venice for a full day of mountain lakes, Cortina d’Ampezzo, Tre Cime views, and the Prosecco Road. An English-speaking driver-guide takes up to eight people by minivan through Veneto, ending with a Valdobbiadene Prosecco DOCG tasting. Guides such as Simone, Miriam, Francesco, and Massimo are praised for their humor, local insight, and thoughtful photo stops.

“Everything was great. We really enjoyed the Proseco area, and of course we were there during the grape harvest, so it was just fascinating. Miles of vineyards loaded down with sweet ripe grapes!”

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10.Franciacorta Winery and Bergamo Day Trip with Lunch

★★★★★★★★★★4.8 · 85 reviews · from $328

Leave Milan by air-conditioned minivan for two hours in Bergamo’s walled upper town, then enjoy a three-course lunch near Lake Iseo. Finish at a historic Franciacorta winery with a sommelier-led tour and two sparkling wine tastings. English-speaking guides such as Nicolò, Elia, and Francesca bring local context to the day.

“It was fantastic.. one of the best days of my entire trip! Nicolo was an amazing guide and everything was perfect, every stop was beautiful.”

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11.San Gimignano & Volterra Day Trip with Food & Wine

★★★★★★★★★★4.7 · 57 reviews · 9.5 hours · from $327

Spend 9.5 hours with a guide such as Luciana, traveling by air-conditioned car from Florence to Volterra and San Gimignano. Walk medieval streets, see Etruscan and alabaster traditions, eat lunch at a winery, taste Vernaccia and Chianti Super Tuscan wines, and try gelato from a world champion maker.

“This was one of our favourite days. Our guide was great and we had a fantastic day”

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12.Tuscany Chianti Winery Private Day-Trip with Lunch

★★★★★★★★★★5.0 · 20 reviews · 6 hours · from $258

Leave Florence with an English-speaking guide such as Gianni, Gionni, or Gio for a six-hour private or small-group trip through Chianti. Visit Greve and Montefioralle, tour a family-run estate, learn about olive oil, and enjoy a Tuscan lunch with three Chianti Classico wines.

“Gianni was truly the best guide I’ve ever had — everything about the experience was perfect. It was so incredible to meet someone who is not only knowledgeable, but also genuinely honest and deeply passionate about Tuscany. He brought the region to life in a way I’ll never forget. I honestly can’t recommend him enough! I’ll be back soon and can’t wait to have him as my guide again.”

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